Category: 766-46-1

Electric Literature of 766-46-1, The chemical industry reduces the impact on the environment during synthesis 766-46-1, name is 2′-Bromophenylacetylene, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of sulfonyl azides 1 (0.6 mmol), o-bromo-phenylacetylenes 2 (0.5 mmol), aromatic amines 3 (0.55 mmol), and CuI (0.05 mmol) in DMSO (2 mL) in Schlenk tube was added TEA (0.5 mmol) slowly via a syringe. The reaction solution was stirred at room temperature under N2 for 2 h. The solution was then added to CuI (0.05 mmol), K2CO3 (1 mmol), and l-proline (0.2 mmol), and the mixture was stirred at 60 C under N2 for 4 h. The reaction mixture was partitioned between ethyl acetate and saturated aq NH4Cl, the organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel with petroleum ether and ethyl acetate (6:1 to 9:1).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2′-Bromophenylacetylene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jin, Hongwei; Zhou, Bingwei; Wu, Zhi; Shen, Yang; Wang, Yanguang; Tetrahedron; vol. 67; 6; (2011); p. 1178 – 1182;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 766-46-1,Some common heterocyclic compound, 766-46-1, name is 2′-Bromophenylacetylene, molecular formula is C8H5Br, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a 10 mL screw cap vial, copper(I) 3-methylsalicylate (5.4 mg, 0.025 mmol), a cold (-20 C.) solution of azidotrifluoromethane in THF (?1.5 mmol, 3-4 mL) and a solution of 2-bromophenylacetylene (1.0 mmol) in THF (0.5 mL) were added. The vial was closed and the content stirred at rt for 18 h. THF was removed under reduced pressure, Et2O (20 mL) was added and the organic phase was washed with aqueous NaHCO3 (5%, 2*10 mL), water (10 mL), aqueous LiCl (1 mol¡¤l-1, 10 mL) and brine (10 mL), dried (MgSO4), filtered and solvent was removed under reduced pressure. Purification by column chromatography (silicagel) gave the product as a yellow oil. Yield 84%; Rf (cyklohexane:EtOAc, 97:3)=0.27; IR (CHCl3, film)=1420, 1206, 1191, 760 cm; 1H NMR (400 MHz, CDCl3) delta=8.63 (s, 1H), 8.16-8.14 (ddd, J=7.8, 1.7, 0.4 Hz, 1H), 7.71-7.69 (ddd, J=8.1, 1.3, 0.4 Hz, 1H), 7.49-7.45 (ddd, J=7.9, 7.4, 1.3 Hz, 1H), 7.31-7.27 (ddd, J=8.1, 7.4, 1.8 Hz, 1H); 13C NMR (101 MHz, CDCl3) delta=146.1, 133.8, 131.0, 130.5, 129.4, 128.0, 121.4, 120.6, 117.7 (q, 1JC-F=268.4 Hz); 19F NMR (376 MHz, CDCl3) delta=-59.2 (s); HRMS (ESI) m/z calculated for C9H6N3F3Br [M+H]+: 291.9692, found 291.9692.

The synthetic route of 766-46-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ustav organicke chemie a biochemie AV CR, v.v.i.; CF Plus Chemicals s.r.o.; BEIER, Petr; MATOUSEK, Vaclav; BLASTIK, Zsofia E.; VOLTROVA, Svatava; (12 pag.)US2019/161452; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 766-46-1, A common heterocyclic compound, 766-46-1, name is 2′-Bromophenylacetylene, molecular formula is C8H5Br, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: To a solution of sulfonyl azides 1 (0.6 mmol), o-bromo-phenylacetylenes 2 (0.5 mmol), aromatic amines 3 (0.55 mmol), and CuI (0.05 mmol) in DMSO (2 mL) in Schlenk tube was added TEA (0.5 mmol) slowly via a syringe. The reaction solution was stirred at room temperature under N2 for 2 h. The solution was then added to CuI (0.05 mmol), K2CO3 (1 mmol), and l-proline (0.2 mmol), and the mixture was stirred at 60 C under N2 for 4 h. The reaction mixture was partitioned between ethyl acetate and saturated aq NH4Cl, the organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel with petroleum ether and ethyl acetate (6:1 to 9:1).

The synthetic route of 766-46-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jin, Hongwei; Zhou, Bingwei; Wu, Zhi; Shen, Yang; Wang, Yanguang; Tetrahedron; vol. 67; 6; (2011); p. 1178 – 1182;,
Bromide – Wikipedia,
bromide – Wiktionary

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 766-46-1, name is 2′-Bromophenylacetylene, A new synthetic method of this compound is introduced below., name: 2′-Bromophenylacetylene

General procedure: All reactions were carried out under aerobic conditions. A mixture of aromatic alkyne (1.0 mmol), AgNO3 (0.075 mmol), Cs2CO3 (1.0 mmol), catalyst compound 1 (0.5 mol %), and n-butyl alcohol/H2O (in 1:2 proportion, 3 mL) was stirred at 60 C for 24 h and then extracted three times with ethyl acetate (3 x 15 mL). The combined organic phase was dried with MgSO4, filtrated, and then solvent was removed on a rotary evaporator. The product was isolated by thin-layer chromatography. The purified products were identified by 1H-NMR and 13C-NMR spectroscopy (Figures S1-S10).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Guo, Mengping; Chen, Bo; Lv, Meiyun; Zhou, Xiuling; Wen, Yongju; Shen, Xiuli; Molecules; vol. 21; 5; (2016);,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 766-46-1, name is 2′-Bromophenylacetylene, molecular formula is C8H5Br, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 766-46-1

For the synthesis of 1e, the title compound 1e? wasprepared as follows. A solution of LDA, prepared from iPr2NH(0.93 mL, 6.5 mmol) and nBuLi (2.7M in hexane, 2.4 mL, 6.5 mmol)in THF (6 mL) at 0 C, was added to a solution of 1-bromo-2-ethynylbenzene [766-46-1] (1.1 g, 5.9 mmol) in THF (6 mL)at 78 C for 30 min tert-Butyldimetylsilyl chloride [18162-48-6](1.1 g, 7.1 mmol) was added to the mixture at that temperature.The reaction mixturewas warmed to room temperature and stirredfor 12 h. After adding aqueous NH4Cl, the aqueous mixture wasextracted with hexane three times. The combined organic phasewas dried over Na2SO4 and evaporated. Purification of the residueby silica-gel column chromatography gave 1-bromo-2-[2-[(1,1-dimethylethyl)dimethyl-silyl]ethynyl]benzene in (1.6 g, 5.4 mmol,92%) as a pale yellow liquid. 1H NMR (400 MHz, CDCl3, 7.26 ppm)d 0.21 (s, 6H), 1.02 (s, 9H), 7.15 (ddd, J 7.6, 7.6, 1.6 Hz, 1H), 7.24(ddd, J 7.6, 7.6, 1.2 Hz, 1H), 7.50 (dd, J 7.6, 1.6 Hz, 1H), 7.57 (dd,J 8.0, 1.2 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 766-46-1, its application will become more common.

Reference:
Article; Kinoshita, Hidenori; Fukumoto, Hiroki; Ueda, Akihiro; Miura, Katsukiyo; Tetrahedron; vol. 74; 14; (2018); p. 1632 – 1645;,
Bromide – Wikipedia,
bromide – Wiktionary